Confessions of an InfoSec Burnout

Soul-crushing failure.

If asked, that is how I would describe the last 10 years of my career, since leaving AOL.

I made one mistake, one bad decision, and it's completely and thoroughly derailed my entire career. Worse, it's unclear if there's any path to recovery as failure piles on failure piles on failure.

The Ground I've Trod

To understand my current state of career decrepitude, as well as how I've seemingly become an industry pariah...

I have worked for 11 different organizations over the past 10 years. I left AOL in September 2007, right before a layoff (I should have waited for the layoff and gotten a package!). I had been there for more than 3.5 years and I was miserable. It was a misery of my own making in many ways. My team manager had moved up the ranks, leaving an opening. All my teammates encouraged me to throw my hat in the ring, but I demurred, telling myself I simply wasn't ready to manage. Oops. Instead, our new manager came through an internal process, and immediately made life un-fun. I left a couple months later.

When I left AOL, it was to take a regional leadership role in BT-INS (BT Global Services - they bought International Network Services to build-out their US tech consulting). A month into the role as security lead for the Mid-Atlantic, where I was billable on day 1, the managing director left and a re-org merged us in with a different region where there was already a security lead. 2 of 3 sales reps left and the remaining person was unable and unwilling to sell security. I sat on the bench for a long time, traveling as needed. An idle, bored Ben is a bad thing.

From BT I took a leadership role with this weird tech company in Phoenix. There was no budget and no staff, but I was promised great things. They let me start remote for a couple months before relocating. I knew it was a bad fit and not a good company before we made the move. I could feel it in my gut. But, I uprooted the family in the middle of the school year (my wife is an elementary teacher) and went to Phoenix, ignoring my gut. 6 months later they eliminated the position. The fact is that they'd hired a new General Counsel who also claimed a security background (he had a CISSP), and thus they made him the CISO. The year was 2009, the economy was in tatters after the real estate bubble had burst. We were stranded in a dead economy and had no place to go.

Thankfully, after a month of searching, someone threw me a life-line and I promptly started a consulting gig with Foreground Security. Well, that was a complete disaster and debacle. We moved back to Northern Virginia and my daughter immediately got sick and ended up in the hospital (she'd hardly had a sniffle before!). By the time she got out of the hospital I was sicker than I'd ever been before. The doctors had me on a couple different antibiotics and I could hardly get out of bed. This entire time the president of the company would call and scream at me every day. Literally, yelling at the top of his lungs over the phone. Hands-down the most unprofessional experience I'd had. The company partnership subsequently fell apart and I was kacked in the process. I remember it clearly to this day: I'm at my parents house in NW MN over the winter holidays and the phone rings. It's the company president, who starts out by telling me they'd finally had the kid they were expecting. And, they're letting me go. Yup, that's how the conversation went ("We had a baby. You're termed.").

Really, being out of Foreground was a relief given how awful it had been. Luckily they relocated us no strings attached, so I didn't owe anything. But, I once again was out of a job for the second time in 3 months. I'd had 3 employers in 2009 and ended the year unemployed.

In early 2010 I was able to land a contract gig, thinking I'd try a solo practice. It didn't work out. The client site was in Utah, but they didn't want to pay for a ton of travel, so I tried working remotely, but people refused to answer the phone or emails, meaning I couldn't do the work they wanted. The whole situation was a mess.

Finally, I connected with Peter Hesse at Gemini Security Solutions to do a contract-to-hire tryout. His firm was small, but had a nice contract with a large client that helped underpin his business. He brought me in to do a mix of consulting and biz dev, but after a year+ of trying to bring in new opportunities (and have them shot down internally for various reasons), I realized that I wasn't going to be able to make a difference there. Plus, being reminded almost daily that I was an expensive resource didn't help. I worked my butt off but in the end it was unappreciated, so I left for LockPath.

The co-founders of LockPath had found me when I was in Phoenix thanks to a paper I'd written on PCI for some random website. They came out to visit me and told me what they were up to. I kept in touch with them over the years, including through their launch of Keylight 1.0 on 10/10/10. I somewhat forced my way into a role with them, initially to build a pro svcs team, but that got scrapped almost immediately and I ended up more in a traveling role, presenting at conferences to help get the name out there, as well as doing customer training. After a year-and-a-half of doing this, they hired a full-time training coordinator who immediately threw me under the bus (it was a major wtf moment). They wanted to consolidate resources at HQ and moving to Kansas wasn't in the cards, so seeing the writing on the wall I started a job search. Things came to an end in mid-May while I was on the road for them. I remember it clearly, having dropped my then-3yo daughter with the in-laws the night before, I had just gotten into my hotel room in St. Paul, MN, ahead of Secure360 and the phone rang. I was told it was over, but he was going to think about it overnight. I asked "Am I still representing the company when I speak at the conference tomorrow?" and got no real answer, but was promised one first thing the next morning. That call never came, so I spoke to a full room the next morning and worked the booth all that day and the morning after that. I met my in-laws for lunch to pick-up my kiddo, and was sitting in the airport awaiting our flight home when the call finally came in delivering the final news. I was pretty burned-out at that time, so in many ways it was welcome news. Startup life can be crazy-intense, and I thankfully maintain a decent relationship with the co-founders today. But those days were highly stressful.

The good news was that I was already in-process with Gartner, and was able to close on the new gig a couple weeks later. Thus started what I thought would be one of my last jobs. Alas, I was wrong. As was much with my time there.

It bears noting here before I go any further an important observation: The onboarding experience is all-important. If you screw it up, then it sets a horrible tone for the entire gig, and the likelihood of success drops significantly. If onboarding is professional and goes smoothly, then people will feel valued and able to contribute. If it goes poorly, then people will feel undervalued from the get-go and they will literally start from an emotional hole. Don't do this to people! I don't care if you're a startup or a Fortune 50 large multi-national. Take care of people from Day 1 and things will go well. Fail at it and you'd might as well stop and release them asap.

Ok, anyway... back to Gartner. It was a difficult beginning. I was assigned a mentor, per their process, but he was gone 6 of the first 9 weeks I was there. I was sent to official "onboarding training" the end of August (the week before Labor Day!) despite having been there for 2 months by that time. I was not prepped at all before going to onboarding, and as it turns out I should have been. Others showed up with documents to be edited and an understanding of the process. I showed up completely stressed out, not at all ready to do the work that was expected, and generally had a very difficult time. It was also the week before Labor Day, which at the time meant it was teacher workshops, and I was on the road for it with 2 young kids at home. Thankfully, the in-laws came and helped out, but suffice to say it was just really not good all-around.

I really enjoyed the manager I worked for initially, but all that changed in February 2014 when my former mentor, with whom I did not at all get along, became the team manager. The stress levels immediately spiked as the focus quickly shifted to strong negativity. I had been struggling to get paper topics approved and was fighting against the reality that the target audience for Gartner research is not the leading edge of thinking, but the middle of the market. It took me nearly a full year to finally get my feet under me and start producing at an appropriate pace. My 1 yr mark roughly corresponded with the mid-year review, which was highly negative. By the end of the year I finally found my stride and had a ton of research in the pipeline (most of which would publish in early 2015). Unfortunately, the team manager, Captain Negative, couldn't see that and gave me one of the worst performance reviews I've ever received. It was hands-down the most insulted I'd ever been by a manager. It seemed very clear from his disrespectful actions that I wasn't wanted there, and so I launched an intensive job search. Meanwhile, I published something like 4 papers in 6 weeks while also having 4 talks picked up for that year's Security & Risk Management Conference. All I heard from my manager was negativity despite all that progress and success. I felt like shit, a total failure. There were no internal opportunities, so outward I looked, eventually landing at K12.

Oh, what a disaster that place was. K12 is hands-down the most toxic environment I've ever seen (and I've seen a lot!). Literally, all 10 people with whom I'd interviewed had lied to me - egregiously! I'd heard rumblings of changes in the executive ranks, but the hiring manager assured me there was nothing that would affect me. A new CIO - my manager's boss - started the same day I did. Yup, nothing that would affect me. Ha. Additionally, it turns out that they already had a "security manager" of sorts working in-house. He wasn't part of the interview process for my "security architect" role. They said they were doing DevOps, but it was just a side pilot that wasn't getting anywhere. Etc. Etc. Etc. Suffice to say, it was really bad. I frankly wondered how they were still in business, especially in light of the constant stream of lawsuits emanating from the states where they had "online public schools." Oy...

Suffice to say, I started looking for work on Day 1 at K12. But, there wasn't much there, and recruiters were loathe to talk to me given such a short stint. Explanations weren't accepted, and I was truly stuck. The longer I was there, the worse it looked. Finally, my old manager from AOL reached out as he was starting a CISO role at Ellucian. He rescued me and in October 2015 I started with them in a security architect role.

There's not much I can say about my experience at Ellucian. Things seemed ok at first, but after a CIO change a few months in, plus a couple other personnel issues, things got wonky, and it became clear my presence was no longer desired. When your boss starts cancelling weekly 1-on-1 meetings with you, it becomes pretty clear that he doesn't really want you there. New Context reached out in May 2016 and offered me an opportunity to do research and publishing for them, so I jumped at it and got the heck out of dodge. It turns out, this was a HUGE mistake, too...

There's even less I can say about New Context... we'll just put it at this: Despite my best efforts, I was never able to get things published due to a lack of internal approvals. After a year of banging my head against the wall, my boss and I concluded it wasn't going to happen, and they let me go a couple weeks later.

From there, I launched my own solo practice and signed what was to be a 20-wk contract with an LA-based client. They had been chasing me for several months to come help them out in a consulting (staff augmentation, really) capacity. I closed the deal with them and started on July 31st of this year. That first week was a mess with them not being ready for me on day 1, then sending me a botched laptop build on day 2, and then finally getting me online on day 3. I flew to LA to be on-site with them the following week and immediately locked horns with the other security architect. That first week on-site was horribly stressful. Things had finally started leveling off last wk, and then yesterday (Monday 8/28/17) they called and cancelled the contract. While I'm disappointed, it's also a bit of a relief. It wasn't a good fit, it was a very difficult client experience, and overall I was actively looking for new opportunities while I did what I could for them.

Shared Culpability or Mea Culpa?

After all these years, I'm tired of taking the blame and being the seemingly constant punchline to some joke I don't get. I'm tired, I'm burned-out, I'm frustrated, I'm depressed, and more than anything I just don't understand why things have gone so completely wrong over the past 10 years. How could one poor decision result in so much career chaos and heartache? It's astonishing. And appalling. And depressing.

I certainly share responsibility in all of this. I tend to be a fairly high-strung person (less so over the years) and onboarding is always highly stressful for me. Increasingly, employers want you engaged and functional on Day 1, even though that is incredibly unrealistic. Onboarding must be budgeted for a minimum of 3-6 months. If a move is involved, then even longer! Yet nobody is willing to allow that any more. I don't know if it's mythology or downward pressure or what... but the expectations are completely unreasonable.

But I do have a responsibility here, and I've certainly not been Mr. Sunshine the past few years, which means I tend to come off as extremely negative and sarcastic, which can be off-putting to people. Attitude is something I need to focus on when starting, and I need to find ways to better manage all the stress that comes with commencing a new gig.

That said, I also seem to have a knack for picking the wrong jobs. This even precedes my time at AOL, which is really a shining anchor in the middle of a turbulent career. Coming into the workforce just before the DOT-COM bubble burst, I've been through lots of layoffs and turmoil. I simply have a really bad track record of making good employment choices. I'm not even sure how to go about fixing that, short of finding people to advise me on the process.

However, lastly, it's important for companies to realize that they're also failing employees. The onboarding process is immensely important. Treating people respectfully and mindfully from Day 1 is immensely important. Setting reasonable expectations is immensely important. If you do not actively work to set your personnel up for success, then it is extremely unlikely that they'll achieve it! And even in this day and age where companies really, truly don't value personnel (except for execs and directors), it must be acknowledged that there is a significant cost in lost productivity, efficiency, and effectiveness that can be directly tied to employee turnover. This includes making sure managers are reasonably well trained and are actually well-suited to being managers. You owe it to your employees to treat them as humans, not just replaceable cogs in a machine.

Where To Go From Here?

The pull of deep depression is ever stronger. Resistance becomes evermore difficult with each successive failure. I feel like I cannot buy a break. My career is completely off-track and I decreasingly see a path to recovery. Every morning is a struggle to get up and look for work yet again. I feel like I've been doing this almost constantly for the past 10 years. I've not been settled anywhere since AOL (maybe BT).

I initially launched a solo practice, Falcon's View Consulting, to handle some contracts. And, that's still out there if I need it. However, what I really need is a full-time job. With a good, stable company. In a role with a good manager. A role that eventually has upward mobility (in order to get back on track).

Where that role is based I really do not care (my family might). Put me in a leadership role, pay me a reasonable salary, and relocate me to where you need me. At this point, I'm willing to go to bat and force the family to move, but you gotta make it easy and compelling. Putting me into financial hardship won't get it done. Putting me into a difficult position with no support won't get it done. Moving me and not being committed to keeping me onboard through the most stressful times won't get it done.

I'm quite seriously at the end of my rope. I feel like I have about one more chance left, after which it'll be bankruptcy and who knows what... I've given just about everything I can to this industry, and my reward has been getting destroyed in the process. This isn't sustainable, it isn't healthy, and it's altogether stupid.

I want to do good work. I want to find an employer that values me that I can stay with for a reasonable period of time. I've never gone into any FTE role thinking "this is just a temporary stop while I find something better." I throw my whole self into my work, which is - I think - why it is so incredibly painful when rejection and failure final happen. But I don't know another way to operate. Nor should anyone else, for that matter.

Two roads diverged in the woods / And I... I took the wrong one / And that has made all the difference

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